Apple Mail (Snow Leopard), Entourage And Exchange: A Brief Review

And now a post on workflow and email. Non-Mac users will be bored, so please feel free to skip this one. Like you don’t always feel free to skip posts. . . .

McGill uses Microsoft’s Exchange Server protocol, which allows people to sync their email, contacts and calendar across platforms, computers, and so forth. The thing is, support for exchange on the Mac has been quite limited until last year. After using a fine email program called Eudora for many years, I switched to Microsoft’s Entourage a few years ago as my administrative duties entangled me in the web of various exchange services.

The problem is that while Entourage has a lot of power, it kind of bites as an email program, at least for how I use email. Entourage is essentially some perverse form of project management software, and that is clearly how it is conceived. At its heart is a massive database that holds all your information, called an identity. The problem is that the identity can’t get very big before bad things happen.

In the productivity world, there is much talk of the Inbox Zero philosophy, which encourages swift and systematic email management. I take the opposite approach, “Inbox Infinity.” I don’t manage my email. If I need to find something, I do a search. Each month, I pull all my email off the server and dump it in a file. My theory is that is takes less time to do this and simply do a search than to figure out where everything should go and what I might need in a few days, weeks or years.

In Entourage, this meant that every couple years, I needed to create a “new identity” so that my database would never get too big. The Entourage database was also a major problem for Time Machine to back up, which meant it had to be backed up manually. And worst of all, on more than one occasion, the database got corrupted, causing me a wide variety of headaches. Some things, like mailing lists, are in fact impossible to either export from Entourage or to back up properly. Entourage also didn’t handle multiple email addresses well. To remedy that I had set up Thunderbird to deal with some IMAP accounts I have on other servers. Inbox Infinity Indeed.

So when I had my every-two-years Entourage crisis a couple weeks back, I decided that instead of fixing it, I would export everything to Apple Mail and try that program, along with iCal and Address book. I would have done it sooner, but I had to wait to upgrade to Snow Leopard (the latest Mac OS) because of all the audio software I use (dozens of programs made by different companies, some quite small, and which often lag behind the main OS by as much as a year in terms of being updated). Before this version of OSX, Apple’s programs did not work with exchange servers.

Configuring Mail for Exchange took a few minutes. Address book and Contacts automatically configured themselves. I then began the process of importing all my old email, which took a few hours but wasn’t something I had to attend to (it was fairly automated; every so often I had to click a couple things). Mail treats each email as an individual file, which means it is much easier for Time Machine to automatically back up old email. It also means that instead of having to switch “identities” if I want to find an email from a few months ago, I can simply do a search now. In fact, I now have a searchable 11 year archive of email on my computer that runs seamlessly. No, I don’t need all those thousands of emails, but 20 gigs or so is nothing compared to the amount of disc space available on a modern laptop (I have about 1 terrabyte of hard drive space on my Macbook Pro). And even if you factor in the time I spent on Entourage hassles over the last few years, that is still less time than I would have spent sorting the stuff out in some more rigorous fashion.

Mail, iCal and Address book are also much easier to use in my everyday tasks: writing emails from one of two accounts, making and changing calendar dates and adding contacts. Entourage made all that stuff fussy and difficult, largely because it had some many different capabilities that you had to navigate through a pool of stuff just to do what you really wanted to do. Mail, iCal and Address Book are certainly less capable and not proper project management software, but for a professor, they work perfectly, and sync effortlessly through Exchange. As an added bonus, Mail feels like Eudora on steroids, which is great because I always preferred its interface to Entourage’s.

After a couple days I was so happy with it that I set Carrie up. One pleasant side effect is that it now became easy for us to see each other’s calendars. For the next year or so this won’t be such a big deal, but it will allow us to make plans and see what the other person is up to.

There you have it. I am sure that Entourage can do things that Apple’s programs cannot, but I have yet to need to do any of those things, and if anything, my professional life should be a little simpler in the coming years rather than more complicated, so the odds of my needing to plunge into the labyrinthine menus of Microsoft’s bloatware email program are fairly low. As if to confirm my own evaluation, Microsoft themselves are discontinuing it in favor of a version of Outlook for Mac. I do not think I will be using it.

All that said, I do have to offer kudos to Microsoft’s telephone technical support (for Education users, anyway). They were absolutely great and knowledgable, and also refreshingly candid about the limitations of their own software — especially the Entourage database. Certainly if I have a problem with Word or some other program, I wouldn’t hesitate to go straight to them instead of starting with on-campus support.

Google and gmail are services, these are mail clients. You can read gmail in thunderbird, entourage or mail. gmail on its own is searchable via a web interface, and google calendar can be synced (I think–it’s a little wonky) but in my case I need access to my university’s exchange servers, so I don’t get a choice in my server technology, so it’s not really a choice. I do have a gmail address but not for work.

I just got my first iMac and really hate the iCal program. The fonts are so small I can barely read them. MS Office was much easier to use. Is there an alternative program you can suggest for mail? I do sync with an iPhone4.

Well, if you prefer Office, why not use Office? Besides Mail and Entourage, I don’t know what syncs with exchange, but if you don’t use an exchange server, you could use any program that you like. It’s all about whatever interface you prefer. In terms of free stuff, Mozilla’s offerings seem pretty good.